GB592631A - Cysteine and cystine - Google Patents
Cysteine and cystineInfo
- Publication number
- GB592631A GB592631A GB827745A GB827745A GB592631A GB 592631 A GB592631 A GB 592631A GB 827745 A GB827745 A GB 827745A GB 827745 A GB827745 A GB 827745A GB 592631 A GB592631 A GB 592631A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- cysteine
- hydrolysis
- alpha
- acids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- XUJNEKJLAYXESH-REOHCLBHSA-N L-cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 title abstract 5
- 235000018417 cysteine Nutrition 0.000 title abstract 5
- 229960003067 Cystine Drugs 0.000 title abstract 3
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine zwitterion Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 title abstract 3
- 229960002433 Cysteine Drugs 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- MGYMHQJELJYRQS-ZJUUUORDSA-N ascaridole Natural products C1C[C@]2(C)OO[C@@]1(C(C)C)C=C2 MGYMHQJELJYRQS-ZJUUUORDSA-N 0.000 abstract 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing Effects 0.000 abstract 2
- 239000011630 iodine Substances 0.000 abstract 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052740 iodine Inorganic materials 0.000 abstract 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 2
- URRCWJIXJMEOET-UHFFFAOYSA-N 2-(5-methoxythiophen-2-yl)ethanethioic S-acid Chemical compound COC1=CC=C(CC(S)=O)S1 URRCWJIXJMEOET-UHFFFAOYSA-N 0.000 abstract 1
- UFDFFEMHDKXMBG-UHFFFAOYSA-N 2-acetamidoprop-2-enoic acid Chemical compound CC(=O)NC(=C)C(O)=O UFDFFEMHDKXMBG-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- 229960001305 Cysteine Hydrochloride Drugs 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Incidol Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H Iron(III) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 abstract 1
- QIJRTFXNRTXDIP-JIZZDEOASA-N [(1R)-1-carboxy-2-sulfanylethyl]azanium;chloride;hydrate Chemical compound O.Cl.SC[C@H](N)C(O)=O QIJRTFXNRTXDIP-JIZZDEOASA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 230000002378 acidificating Effects 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- -1 acylamino acrylic acid Chemical compound 0.000 abstract 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic S-acid Chemical class SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000001264 neutralization Effects 0.000 abstract 1
- 230000003472 neutralizing Effects 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000001590 oxidative Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cysteine is produced by adding a thiocarboxylic acid to an alpha-acylamino-acrylic acid or a hydrolysable functional derivative thereof, e.g. a salt, amide, ester, nitrile, acid halide or acid anhydride and then hydrolysing the resulting N : S-diacyl cysteine or hydrolysable functional derivative thereof. The cysteine may be oxidized either simultaneously with the hydrolysis step or subsequently, to cystine. The reaction may be carried out in an inert solvent such as benzene or ether or an excess of thio acid may be used as solvent. Mild heating and the presence of a catalyst such as benzoyl peroxide or ascaridole are advantageous. Any suitable hydrolysing agent may be used such as mild alkalies, e.g. alkali carbonates or alkaline earth oxides, acids, &c., but neutral or acidic conditions are preferred. Hydrolysis may also be carried out in aqueous or partiallyaqueous media, e.g. aqueous methyl alcohol. Suitable oxidizing agents are, e.g. oxygen, iodine, bromine, hydrogen peroxide and ferric sulphate. Either of the two tautomeric forms of the alpha acylamino acrylic acid may be used. In an example thio-acetic acid is added to alpha acetylamino acrylic acid, ascaridole being used as catalyst. N : S-diacetylcysteine is obtained by refluxing the mixture and then evaporating under reduced pressure and is converted to cystine by hydrolysis with concentrated hydrochloric acid under oxidizing conditions using iodine in methanol. Cysteine may be isolated by carrying out the hydrolysis, e.g. with dilute hydrochloric acid and neutralizing the cysteine hydrochloride obtained. Other thio acids such as thiopropionic, thiobutyric and thiobenzoic acids may be used.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB592631A true GB592631A (en) | 1947-09-24 |
Family
ID=1629283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB827745A Expired GB592631A (en) | 1945-04-04 | Cysteine and cystine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB592631A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4934969B1 (en) * | 1968-06-11 | 1974-09-19 | ||
| US5487886A (en) * | 1989-10-10 | 1996-01-30 | The Gillette Company | Amino acid β-lyase enzyme inhibitors as deodorants |
| US5648513A (en) * | 1993-09-09 | 1997-07-15 | Laney; Judith Wolfe | O-acyl serines |
| US5650538A (en) * | 1991-11-29 | 1997-07-22 | Astra Aktiebolag | Organic salts of N,N'-diacetyl cystine |
| US5800804A (en) * | 1993-09-09 | 1998-09-01 | The Gillette Company | O-acyl serines and threonines as deodorants |
-
1945
- 1945-04-04 GB GB827745A patent/GB592631A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4934969B1 (en) * | 1968-06-11 | 1974-09-19 | ||
| US5487886A (en) * | 1989-10-10 | 1996-01-30 | The Gillette Company | Amino acid β-lyase enzyme inhibitors as deodorants |
| US5650538A (en) * | 1991-11-29 | 1997-07-22 | Astra Aktiebolag | Organic salts of N,N'-diacetyl cystine |
| US5693858A (en) * | 1991-11-29 | 1997-12-02 | Astra Aktiebolag | Organic salts of N,N'-diacetyl cystine |
| US5648513A (en) * | 1993-09-09 | 1997-07-15 | Laney; Judith Wolfe | O-acyl serines |
| US5800804A (en) * | 1993-09-09 | 1998-09-01 | The Gillette Company | O-acyl serines and threonines as deodorants |
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